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Polymer, curable resin composition, cured product, and article

a technology of curable resin and polymer, applied in the field of polymer, curable resin composition, cured product, and article, can solve the problems of difficult to obtain a high molecular weight, limited application, and disadvantages of industrial level manufacturing, and achieves simple manner, high surface hardness, and high molecular weight polymer

Active Publication Date: 2013-03-19
NIPPON SHOKUBAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about a new polymer (A) that can be used to produce high molecular weight polymers without using active metal complexes or low temperatures. This polymer contains a specific unsaturated group that can be easily cured to produce a durable, high-quality coating on plastic and film substrates. The cured coating has excellent hardness, resistance to scratching, and adhesion to the substrate. It also has good light transmission. The polymer can be easily obtained by polymerizing specific vinyl monomers and cyclic ether compounds.

Problems solved by technology

In the case of production by a cationic polymerization method, a polymer having higher molecular weight is obtained generally by carrying out the reaction at lower temperature, however, it is known that, for obtaining a polymer having a molecular weight of several thousand or more, setting of the reaction condition to adjust the reaction temperature to 0° C. or lower, in some cases, causing a disadvantage for manufacturing in industrial level.
It is difficult to obtain a high molecular weight polymer, and a molecular design in accordance with the purpose thereof is difficult as compared with an anionic polymerization method and a radical polymerization method, thus, its applicable use is limited.
However, in the living cationic polymerization method as described above, industrial manufacturing is difficult since a very highly active metal complex is usually used as the Lewis acid catalyst.
However, in the case of production of the above-described polymer by the above-described methods (1) to (3), a radical reactive unsaturated group is not introduced completely into a side chain, and a substituent having reactivity remains also after addition of a radical reactive unsaturated group, and depending on its use, there is a possibility of exerting a bad influence, and the number of processes increases, causing a problem in productivity, in some cases.

Method used

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  • Polymer, curable resin composition, cured product, and article
  • Polymer, curable resin composition, cured product, and article
  • Polymer, curable resin composition, cured product, and article

Examples

Experimental program
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Effect test

example 1

[0130]Into a four-necked flask equipped with a stirring bar, thermometer, dropping funnel and nitrogen / air mixed gas line was added 80 g of ethyl acetate, and this was heated up to 40° C. After rising of temperature, a mixture of 128 g of 2-(2-vinyloxyethoxy)ethyl acrylate (VEEA) and 72 g of 2,3-dihydrofuran (DHF), and a dissolved mixture of 13 g of ethyl acetate and 13 mg of phosphotungstic acid were dropped respectively over a period of 2 hours, and polymerization thereof was carried out. After completion of the polymerization, triethylamine was added to stop the reaction.

[0131]Next, the polymer solution was concentrated by an evaporator, then, a polymer (P(VEEA / DHF)-1) as the polymer (A) was obtained. The reaction rate of monomers was found to be 99.1%, by analyzing the mixed solution after stop of the reaction by gas chromatography (GC). The resultant polymer (P(VEEA / DHF)-1) had a number average molecular weight (Mn) of 9840 and a molecular weight distribution (Mw / Mn) of 1.97.

example 2

[0132]Into a four-necked flask equipped with a stirring bar, thermometer, dropping funnel and nitrogen / air mixed gas line was added 80 g of ethyl acetate, and this was heated up to 20° C. After rising of temperature, a mixture of 81 g of VEEA, 109 g of cyclohexyl vinyl ether (CHVE) and 10 g of DHF, and a dissolved mixture of 13 g of ethyl acetate and 13 mg of phosphotungstic acid were dropped respectively over a period of 2 hours, and polymerization thereof was carried out. After completion of the polymerization, triethylamine was added to stop the reaction.

[0133]Next, the polymer solution was concentrated by an evaporator, then, a polymer (P(VEEA / CHVE / DHF)-1) was obtained. The reaction rate of monomers was found to be 99.1%, by analyzing the mixed solution after stop of the reaction by gas chromatography (GC). The resultant polymer (P(VEEA / CHVE / DHF)-1) had a number average molecular weight (Mn) of 8060 and a molecular weight distribution (Mw / Mn) of 1.66.

example 3

[0134]Into a four-necked flask equipped with a stirring bar, thermometer, dropping funnel and nitrogen / air mixed gas line was added 80 g of ethyl acetate, and this was heated up to 20° C. After rising of temperature, a mixture of 196 g of VEEA and 4 g of DHF, and a dissolved mixture of 13 g of ethyl acetate and 13 mg of phosphotungstic acid were dropped respectively over a period of 2 hours, and polymerization thereof was carried out. After completion of the polymerization, triethylamine was added to stop the reaction.

[0135]Next, the polymer solution was concentrated by an evaporator, then, a polymer (P(VEEA / DHF)-2) was obtained. The reaction rate of monomers was found to be 99.0%, by analyzing the mixed solution after stop of the reaction by gas chromatography (GC). The resultant polymer (P(VEEA / DHF)-2) had a number average molecular weight (Mn) of 9800 and a molecular weight distribution (Mw / Mn) of 2.50.

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Abstract

A polymer which has a radical polymerizable unsaturated group in a side chain and can be made a molecular design suitable for the purpose; a curable resin composition containing the polymer, which provides a cured product having high surface hardness after curing and hardly suffering from scratch; the cured product; and an article obtained by laminating the cured product are provided.The polymer (A) of the present invention is obtained by polymerizing, at least, a vinyl monomer represented by the following general formula (1) and a cyclic ether compound represented by the following general formula (2).The polymer (A) of the present invention is preferably obtained by polymerization of 1 wt % or more and 99.9 wt % or less of a vinyl monomer represented by the general formula (1), 0.1 wt % or more and 99 wt % or less of a cyclic ether compound represented by the general formula (2) and 0 wt % or more and 98.9 wt % or less of the other cationic polymerizable monomer.[wherein R1 represents an alkylene group having 2 to 8 carbon atoms, R2 represents a hydrogen atom or a methyl group, and m represents a positive integer][wherein n represents an integer of 1 to 5].

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a National Phase filing under 35 U.S.C. §371 of PCT / JP2009 / 054063 filed on Mar. 4, 2009; and this application claims priority to Application No. 2008055307 filed in France on Mar. 5, 2008 under 35 U.S.C. §119; the entire contents of all are hereby incorporated by reference.TECHNICAL FIELD[0002]The present invention relates to a polymer having a radical polymerizable unsaturated group in a side chain, a curable resin composition containing the polymer, which enables formation of a cured film having excellent low warpage property, abrasion resistance and adhesion when, for example, applied on a plastic base material and cured and laminated thereon, a cured product obtained by curing the curable resin composition, and an article obtained by laminating the cured product.BACKGROUND ART[0003]A polymer of a vinyl ether-type monomer can be produced usually by carrying out a polymerization reaction by a cationic polymerization ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08F24/00C08F22/20
CPCC08F216/165C08F220/40C08F290/142
Inventor MATSUDA, YASUHIROKONOSU, OSAMU
Owner NIPPON SHOKUBAI CO LTD